The Reboot Weekend

Nov 5-7, 2021
Reset, reconnect, and build inner resilience.

Know you're not alone. Join us for our The Reboot Weekend.


  • "Taking time to crack our hearts open allows us all to be the best version of ourselves. Reboot is masterful at accessing the soul of leaders to amplify their impact on the World. Don’t wait, run to be part of the Reboot community!"

    Erik Mitisek

    Erik Mitisek

    Founder & CEO of Highwing

  • "The Reboot Weekend is a total game-changer. It inspired me to do the deep personal work I had been struggling to do alone, and gave me a new perspective on the challenges I am facing as a student and the leader of an organization. Extremely well planned and executed by the Reboot team!"

    Jeremy Scharf

    Jeremy Scharf

    Co-President, MIT Mindfulness & Leadership

  • "Reboot Weekend feels like the golden ticket, the Polar Express suddenly arriving with room for you aboard. Welcomed into the world of reflection and other ways to see, you return home with the ability to hear the bell forever."

    “All aboard,” the conductor cried out. I ran up to him. “Well, he said, “are you coming?” - C. Van Allsburg. The Polar Express.

    Jennifer Byrne

    Jennifer Byrne

    Founder, Jennifer Byrne Photography

  • "I was exhausted from the grind of the year and doubting my desire to continue in my role. The Reboot Weekend introduced me to some tools that aided my reflections and grounded me again. While not ‘magically’ fixed, I am more ready to lead again with conviction and enthusiasm. Give it a shot with an open mind and heart and I think you’ll be better for it.”

    Nelson Rodriguez

    Nelson Rodriguez

    President, Chicago Fire FC

  • "The Reboot Weekend was an incredible and empowering experience. Guided by an exceptional team of caring individuals I was able to detach from the burdens of leadership and finally engage with it. The experience left me with clarity of self, in the path forward, and most importantly, with a community. The Reboot Weekend provides the space and opportunity for leaders to engage with their whole selves while being supported by an extraordinary community."

    Mark Vendramin

    Mark Vendramin

    Managing Director, Properly Investments

  • “Reboot was a unique experience that I can recommend to any founder. Founders experience unique shared challenges across all stages of the company. Being in a group of amazingly self-aware founders who were willing to open up to the group about their struggles and, most importantly, listen to each other’s struggles was incredibly humbling. It takes courage to face your own struggles but there is no better partner than Reboot to help you start that journey. I loved every second of it.”

    Laura Behrens Wu

    Laura Behrens Wu

    CEO of Shippo

  • “I went to the bootcamp to improve my leadership style, but I improved my life instead. The bootcamp is that great and worth every penny. A life-transforming experience.”

    Amir Salihefendic

    Amir Salihefendic

    CEO at Doist

It’s been a tough season for leaders, not to mention the world at large.

Some parts of the world are shifting back to pre-pandemic ways of life, while others continue to deal with the challenges and restrictions this time has brought. Regardless of context, many of the folks we work with and hear from continue to deal with exhaustion and burnout. For those returning to some semblance of normalcy, the challenges of moving beyond a year’s worth of trauma are harrowing. 

Taking care of our teams, our families, our communities—doing what we can to help keep those around us healthy, and thriving. In the midst of these noble pursuits, we can forget to tend to our own wellbeing. 

Once again this fall, the Reboot team will be facilitating a virtual retreat designed to help leaders reset, reconnect with themselves and others, and build inner resilience–the second annual Reboot Weekend. 

Join us for a unique experience that combines remotely facilitated time in nature (e.g. the woods, a park, or even your own backyard), resilience practices, coaching exercises, and fellowship with other leaders doing their best to lead with strength, grace, and authenticity.

The Reboot Weekend is like putting on your own oxygen mask—providing a surge of nourishment and energy to lead your team and organization through whatever this season is presenting.

You will leave with a greater awareness of the personal leadership habits and strategies for being the leader you want to be.


You +15-20 other leaders will be led by a team of Reboot facilitators scattered across the US.


November 5 – 7th. The program begins at 6pm ET on Friday evening and runs until about 9pm. Saturday activities will convene at 10am ET and end at 6pm (with breaks built in). Closing session will be Sunday morning at 10am ET.


Wherever you are! You’ll need a quiet, private spot for video calls. You’ll also have the opportunity to connect from a spot in nature on Saturday morning (this can be the woods, a park, or even your backyard. The only requirement is cell phone service).


The program cost is $2500.* Scholarships are available.


Eligibility & Fit

Are you eligible for The Reboot Weekend? Here are some basic requirements:

  • You’re a CEO/founder/leader in a startup or scaling organization
  • You’ve logged immeasurable hours and have made tremendous sacrifices.
  • You’ve had success with your company. You realize there is more to this game than “success.”
  • You may be tired, but you must be vulnerable, curious and courageous.

Is The Reboot Weekend a fit for you?
If you’re coming to network with other leaders, drum up business, party, or only solve the practical pragmatic problems in your business, The Weekend is not for you.

  • Feel the need to address the problems in your leadership that seem to repeat themselves time and time again.
  • Can’t see clearly why you’re struggling.
  • Want to really understand how you’re being complicit in creating what you say you don’t want.
  • Want to explore how that which has gotten you here, may be keeping you small now, and if it’s time to change.

Reboot clients are ready to transform their lives and leadership…

  • They have a willingness to explore their own agency in bringing about change their lives.
  • They realize that living by everyone else’s rules and ideas is not going to scale, and they want to start leading from within (while paying attention to the lessons of those that have gone before them).
  • They often come to us when they are exhausted and depleted, and they are beginning to see that in order to scale themselves and their organizations they will have to become a different type of leader.
  • They care about more than just financial metrics–they hold a bigger frame when it comes to the concepts of success and a what constitutes a well-lived life.
  • They are ready to do the work of self-actualization and traverse all the hills and valleys in the process. They are willing to be open and vulnerable and to explore their unsorted baggage.


  • are interested in the root cause of patterns and understand how it’s important to break those patterns in order to grow.
  • are eager and ready to explore their own perspective and are deeply curious and are open to looking at things in different ways.
  • want to talk as much about the inner experience as they do with the outer.
  • are interested in learning about themselves and how they can think about building a stronger more sustainable organization.
  • are self-aware, who is willing to go deep, to be emotionally vulnerable, to be curious, to be willing to visit the past with an open curiosity.

Apply for the Reboot Weekend